File:Vancomycin_structure.svg · Wikimedia Commons · See Wikimedia Commons
Vancomycin
Sign in to saveAlso known as (2.2Sp,3.5sa,2.6sp)-O(4.2),C(3.4), Vancocin, c(5.4),O(4.6), Vancomycinum, Vancomicina, Vancomycine
chemische Verbindung
OverviewAI-generated
Vancomycin is a chemical compound with the formula C₆₆H₇₅Cl₂N₉O₂₄. It has a mass of 1447.43 and a defined daily dose of 2. The substance carries a charge of 0 and features an xlogp value of -2.6. Its topological polar surface area is 530, with 19 hydrogen bond donors and 26 hydrogen bond acceptors.
The compound is associated with the NCI Thesaurus ID C925 and MCN codes 3003.20.71 and 3004.20.71. A search for vancomycin on PubMed yields 43478 results. The subject is referenced by 431 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C66H75Cl2N9O24
- Molecular weight
- 1449.2 g/mol
- IUPAC name
- (1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
- SMILES
- C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
- InChIKey
- MYPYJXKWCTUITO-LYRMYLQWSA-N
- XLogP
- -2.6
- Polar surface area
- 530 Ų
- H-bond donors
- 19
- H-bond acceptors
- 26
- Formal charge
- 0
via PubChem
Research
43,478 papers- Vancomycin.Mayo Clinic proceedings · 1991
- Renaissance of vancomycin: approaches for breaking antibiotic resistance in multidrug-resistant bacteria.Canadian journal of microbiology · 2020
- The pharmacokinetic and pharmacodynamic properties of vancomycin.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2006
- Vancomycin mimicry: towards new supramolecular antibiotics.Organic & biomolecular chemistry · 2022
- Vancomycin.The Medical clinics of North America · 1995
via PubMed
Article · Deutsch
Vancomycin ist ein Antibiotikum aus der Wirkstoffgruppe der Glykopeptid-Antibiotika. Es wurde 1955 aus Kulturen von Amycolatopsis orientalis (Streptomyces orientalis) isoliert, und ab 1980 als wirksame Alternative gegen multiresistente Staphylokokken eingesetzt. Staphylokokken kommen neben Enterokokken häufig in Krankenhäusern als Verursacher nosokomialer Infektionen vor. Vancomycin ist ein Antibiotikum der dritten Linie, das eingesetzt wird, wenn andere Mittel aufgrund von Resistenz nicht mehr wirksam sind. Vom Darm wird es nicht aufgenommen, was man sich bei der antibiotikaassoziierten Kolitis zunutze machen kann.
Abstract from DBpedia / Wikipedia · CC BY-SA